CA3073637A1 - Nouveaux composes heterocycliques fongicides - Google Patents
Nouveaux composes heterocycliques fongicides Download PDFInfo
- Publication number
- CA3073637A1 CA3073637A1 CA3073637A CA3073637A CA3073637A1 CA 3073637 A1 CA3073637 A1 CA 3073637A1 CA 3073637 A CA3073637 A CA 3073637A CA 3073637 A CA3073637 A CA 3073637A CA 3073637 A1 CA3073637 A1 CA 3073637A1
- Authority
- CA
- Canada
- Prior art keywords
- piperidin
- thiazol
- dihydroisoxazol
- alkyl
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 230000000855 fungicidal effect Effects 0.000 title description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 283
- 239000000203 mixture Substances 0.000 claims abstract description 103
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- -1 cyano, hydroxy Chemical group 0.000 claims description 284
- 241000196324 Embryophyta Species 0.000 claims description 205
- 125000001424 substituent group Chemical group 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 54
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 53
- 235000013399 edible fruits Nutrition 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 244000005700 microbiome Species 0.000 claims description 26
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 230000003032 phytopathogenic effect Effects 0.000 claims description 20
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 235000013339 cereals Nutrition 0.000 claims description 15
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 13
- 240000008042 Zea mays Species 0.000 claims description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 235000010469 Glycine max Nutrition 0.000 claims description 12
- 244000068988 Glycine max Species 0.000 claims description 12
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 240000003768 Solanum lycopersicum Species 0.000 claims description 11
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 11
- 235000015097 nutrients Nutrition 0.000 claims description 11
- 235000013311 vegetables Nutrition 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- 229920000742 Cotton Polymers 0.000 claims description 10
- 241000219146 Gossypium Species 0.000 claims description 10
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 9
- 241000238631 Hexapoda Species 0.000 claims description 9
- 240000007594 Oryza sativa Species 0.000 claims description 9
- 235000007164 Oryza sativa Nutrition 0.000 claims description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 9
- 235000005822 corn Nutrition 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 235000009566 rice Nutrition 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 8
- 240000007154 Coffea arabica Species 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 8
- 244000061176 Nicotiana tabacum Species 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 235000020971 citrus fruits Nutrition 0.000 claims description 8
- 235000016213 coffee Nutrition 0.000 claims description 8
- 235000013353 coffee beverage Nutrition 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 7
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 7
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 241000238876 Acari Species 0.000 claims description 7
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 7
- 241000244206 Nematoda Species 0.000 claims description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 7
- 244000061456 Solanum tuberosum Species 0.000 claims description 7
- 235000021536 Sugar beet Nutrition 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000005648 plant growth regulator Substances 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 6
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 241000207199 Citrus Species 0.000 claims description 6
- 241000219104 Cucurbitaceae Species 0.000 claims description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
- 241001466451 Stramenopiles Species 0.000 claims description 6
- 241000219094 Vitaceae Species 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 229940088710 antibiotic agent Drugs 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 230000000853 biopesticidal effect Effects 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 6
- 239000012634 fragment Substances 0.000 claims description 6
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- 239000005645 nematicide Substances 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 5
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims description 5
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 240000000111 Saccharum officinarum Species 0.000 claims description 5
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 5
- 244000299461 Theobroma cacao Species 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 239000003337 fertilizer Substances 0.000 claims description 5
- 235000021021 grapes Nutrition 0.000 claims description 5
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 5
- NIXKBAZVOQAHGC-UHFFFAOYSA-M phenylmethanesulfonate Chemical compound [O-]S(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-M 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 235000013616 tea Nutrition 0.000 claims description 5
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
- 235000002566 Capsicum Nutrition 0.000 claims description 4
- 206010061217 Infestation Diseases 0.000 claims description 4
- 241000758706 Piperaceae Species 0.000 claims description 4
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 241000233654 Oomycetes Species 0.000 claims description 3
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 claims description 3
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 claims description 3
- 241000869417 Trematodes Species 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 235000001046 cacaotero Nutrition 0.000 claims description 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 claims description 2
- 125000006802 (C2-C6) alkynylamino group Chemical group 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005109 alkynylthio group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005555 sulfoximide group Chemical group 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 2
- 229910020008 S(O) Inorganic materials 0.000 claims 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 3
- CWKCGHQAARNOGC-UHFFFAOYSA-N [3-chloro-2-[3-[2-[1-[2-[3-(trifluoromethyl)pyridin-2-yl]sulfanylacetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]phenyl]methanesulfonic acid Chemical compound OS(=O)(=O)Cc1cccc(Cl)c1C1CC(=NO1)c1csc(n1)C1CCN(CC1)C(=O)CSc1ncccc1C(F)(F)F CWKCGHQAARNOGC-UHFFFAOYSA-N 0.000 claims 2
- 244000045561 useful plants Species 0.000 claims 2
- XNHXFOUARRXAHV-UHFFFAOYSA-N 1-[4-[2-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]pyridin-4-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C1=NC=CC(=C1)C1CCN(CC1)C(COC1=NC=CC=C1C(F)(F)F)=O XNHXFOUARRXAHV-UHFFFAOYSA-N 0.000 claims 1
- MGURPCSIGKFZPR-UHFFFAOYSA-N 1-[4-[4-(1,5-dihydro-2,4-benzodioxepin-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound C1OC(OCC2=C1C=CC=C2)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C(F)(F)F)=O MGURPCSIGKFZPR-UHFFFAOYSA-N 0.000 claims 1
- WLADFIUGPMGDNL-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC(=C1)Cl)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C(F)(F)F)=O WLADFIUGPMGDNL-UHFFFAOYSA-N 0.000 claims 1
- WXEMHMFMNCTNTK-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]sulfanylethanone Chemical compound FC(F)(F)C1=CC=CN=C1SCC(=O)N1CCC(CC1)C1=NC(=CS1)C1=NOC(C1)C1=C(Cl)C=C(Cl)C=C1Cl WXEMHMFMNCTNTK-UHFFFAOYSA-N 0.000 claims 1
- HRDUBIWZSNUWMO-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[4-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC(=C1)Cl)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC(=C1)C(F)(F)F)=O HRDUBIWZSNUWMO-UHFFFAOYSA-N 0.000 claims 1
- QUNIKSBNYLZHEN-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC(=C1)Cl)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=C(C=C1)C(F)(F)F)=O QUNIKSBNYLZHEN-UHFFFAOYSA-N 0.000 claims 1
- QXNPISYWAWEUGS-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]sulfanylethanone Chemical compound FC(F)(F)C1=CN=C(SCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(Cl)C=C(Cl)C=C2Cl)C=C1 QXNPISYWAWEUGS-UHFFFAOYSA-N 0.000 claims 1
- WCLZSPLOECEXON-UHFFFAOYSA-N 1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[6-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC(F)(F)C1=CC=CC(OCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(Cl)C=C(Cl)C=C2Cl)=N1 WCLZSPLOECEXON-UHFFFAOYSA-N 0.000 claims 1
- UACVDCAYFWXLBT-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-(3-methylpyridin-2-yl)oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C)=O UACVDCAYFWXLBT-UHFFFAOYSA-N 0.000 claims 1
- PGYLHPLXVLBZGB-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NN(C(=C1)C(F)(F)F)C)=O PGYLHPLXVLBZGB-UHFFFAOYSA-N 0.000 claims 1
- ROFPACDWSHWVAH-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=CC(=NN1C)C(F)(F)F)=O ROFPACDWSHWVAH-UHFFFAOYSA-N 0.000 claims 1
- CCOYUPXKUSKXME-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(difluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C(F)F)=O CCOYUPXKUSKXME-UHFFFAOYSA-N 0.000 claims 1
- MAKJRQKVNWDXRD-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C(F)(F)F)=O MAKJRQKVNWDXRD-UHFFFAOYSA-N 0.000 claims 1
- WXYANALBFMTPHS-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[4-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC(F)(F)C1=CC(OCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(Cl)C=CC=C2Cl)=NC=C1 WXYANALBFMTPHS-UHFFFAOYSA-N 0.000 claims 1
- YUFKCRGFTGIOKU-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(difluoromethyl)-1-methylpyrazol-3-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NN(C(=C1)C(F)F)C)=O YUFKCRGFTGIOKU-UHFFFAOYSA-N 0.000 claims 1
- UFGDDBYPSCOHQL-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=C(C=C1)C(F)(F)F)=O UFGDDBYPSCOHQL-UHFFFAOYSA-N 0.000 claims 1
- JSOKZTHDGLRUKG-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]sulfanylethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(CSC1=NC=C(C=C1)C(F)(F)F)=O JSOKZTHDGLRUKG-UHFFFAOYSA-N 0.000 claims 1
- ULKXILBCQZYORK-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=C(C=C1C(F)(F)F)C)=O ULKXILBCQZYORK-UHFFFAOYSA-N 0.000 claims 1
- ZMOPZSGKSNBSAO-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[6-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC(F)(F)C1=CC=CC(OCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(Cl)C=CC=C2Cl)=N1 ZMOPZSGKSNBSAO-UHFFFAOYSA-N 0.000 claims 1
- WTRHFDFUKZMKNS-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[6-methyl-3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound ClC1=C(C(=CC=C1)Cl)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC(=CC=C1C(F)(F)F)C)=O WTRHFDFUKZMKNS-UHFFFAOYSA-N 0.000 claims 1
- UIUQPTTYDGYTDV-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[[5-(trifluoromethyl)pyridin-2-yl]amino]ethanone Chemical compound FC(F)(F)C1=CN=C(NCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(Cl)C=CC=C2Cl)C=C1 UIUQPTTYDGYTDV-UHFFFAOYSA-N 0.000 claims 1
- GALHAHSVXMHAIN-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-(1-methylpyrazol-3-yl)oxyethanone Chemical compound CN1C=CC(OCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(F)C=CC=C2F)=N1 GALHAHSVXMHAIN-UHFFFAOYSA-N 0.000 claims 1
- ZWNHAEIRBPRZKR-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-(3-methylpyridin-2-yl)oxyethanone Chemical compound FC1=C(C(=CC=C1)F)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC=C1C)=O ZWNHAEIRBPRZKR-UHFFFAOYSA-N 0.000 claims 1
- YFXWMUZKSADLKT-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxyethanone Chemical compound CN1N=C(OCC(=O)N2CCC(CC2)C2=NC(=CS2)C2=NOC(C2)C2=C(F)C=CC=C2F)C=C1C(F)(F)F YFXWMUZKSADLKT-UHFFFAOYSA-N 0.000 claims 1
- ZCCBHXOVXRIWMK-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxyethanone Chemical compound CN1N=C(C=C1OCC(=O)N1CCC(CC1)C1=NC(=CS1)C1=NOC(C1)C1=C(F)C=CC=C1F)C(F)(F)F ZCCBHXOVXRIWMK-UHFFFAOYSA-N 0.000 claims 1
- IKANKLLWMQOCDL-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]sulfanylethanone Chemical compound FC1=CC=CC(F)=C1C1CC(=NO1)C1=CSC(=N1)C1CCN(CC1)C(=O)CSC1=NC=CC=C1C(F)(F)F IKANKLLWMQOCDL-UHFFFAOYSA-N 0.000 claims 1
- QPGNDIHOVBKAKC-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[4-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=C(C(=CC=C1)F)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=CC(=C1)C(F)(F)F)=O QPGNDIHOVBKAKC-UHFFFAOYSA-N 0.000 claims 1
- WPFDTYLVCKRJKH-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=C(C(=CC=C1)F)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=C(C=C1)C(F)(F)F)=O WPFDTYLVCKRJKH-UHFFFAOYSA-N 0.000 claims 1
- NSIDMHDPBOIOJC-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-(trifluoromethyl)pyridin-2-yl]sulfanylethanone Chemical compound FC1=CC=CC(F)=C1C1CC(=NO1)C1=CSC(=N1)C1CCN(CC1)C(=O)CSC1=NC=C(C=C1)C(F)(F)F NSIDMHDPBOIOJC-UHFFFAOYSA-N 0.000 claims 1
- DZFPJAWBFQJNMP-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=C(C(=CC=C1)F)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC=C(C=C1C(F)(F)F)C)=O DZFPJAWBFQJNMP-UHFFFAOYSA-N 0.000 claims 1
- AFSRLSGOGMGSMX-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[6-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=CC=CC(F)=C1C1CC(=NO1)C1=CSC(=N1)C1CCN(CC1)C(=O)COC1=NC(=CC=C1)C(F)(F)F AFSRLSGOGMGSMX-UHFFFAOYSA-N 0.000 claims 1
- VBRRLNRZPISAAB-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[6-methyl-3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=C(C(=CC=C1)F)C1CC(=NO1)C=1N=C(SC=1)C1CCN(CC1)C(COC1=NC(=CC=C1C(F)(F)F)C)=O VBRRLNRZPISAAB-UHFFFAOYSA-N 0.000 claims 1
- LETKAWLJHLWZJJ-UHFFFAOYSA-N 1-[4-[4-[5-(2-fluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC1=C(C=CC=C1)C1CC(=NO1)C1=CSC(=N1)C1CCN(CC1)C(=O)COC1=NC=CC=C1C(F)(F)F LETKAWLJHLWZJJ-UHFFFAOYSA-N 0.000 claims 1
- WTGCBXXHBJUGEV-UHFFFAOYSA-N 1-[4-[4-[5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-(trifluoromethyl)pyridin-2-yl]oxyethanone Chemical compound FC(F)(F)C1=CC=CC(=C1)C1CC(=NO1)C1=CSC(=N1)C1CCN(CC1)C(=O)COC1=NC=CC=C1C(F)(F)F WTGCBXXHBJUGEV-UHFFFAOYSA-N 0.000 claims 1
- RTOZRRHQBRJHKH-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]propan-1-one Chemical compound ClC1=C(OC(C(=O)N2CCC(CC2)C=2SC=C(N=2)C2=NOC(C2)C2=C(C=C(C=C2Cl)Cl)Cl)C)C=CC(=C1)Cl RTOZRRHQBRJHKH-UHFFFAOYSA-N 0.000 claims 1
- OWBSNQWNJCREGJ-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]propan-1-one Chemical compound ClC1=C(OC(C(=O)N2CCC(CC2)C=2SC=C(N=2)C2=NOC(C2)C2=C(C=CC=C2Cl)Cl)C)C=CC(=C1)Cl OWBSNQWNJCREGJ-UHFFFAOYSA-N 0.000 claims 1
- PXMUMFJCIFUKEX-UHFFFAOYSA-N 2-(3-methylpyridin-2-yl)oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC=1C(=NC=CC=1)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl PXMUMFJCIFUKEX-UHFFFAOYSA-N 0.000 claims 1
- YCVYWVOYVDBKQU-UHFFFAOYSA-N 2-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CN1N=C(C=C1C(F)(F)F)OCC(=O)N1CCC(CC1)C=1SC=C(N1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl YCVYWVOYVDBKQU-UHFFFAOYSA-N 0.000 claims 1
- GRZWFHOILGYZTD-UHFFFAOYSA-N 2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CN1N=C(C=C1OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl)C(F)(F)F GRZWFHOILGYZTD-UHFFFAOYSA-N 0.000 claims 1
- ALYZLERTOHCLHG-UHFFFAOYSA-N 2-[3-(difluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=CC=CN=C1OCC(=O)N1CCC(CC1)C1=NC(=CS1)C1=NOC(C1)C1=C(Cl)C=C(Cl)C=C1Cl ALYZLERTOHCLHG-UHFFFAOYSA-N 0.000 claims 1
- SAFUGFVPLNULPM-UHFFFAOYSA-N 2-[3-(difluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound FC(C=1C(=NC=CC=1)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1F)F)F SAFUGFVPLNULPM-UHFFFAOYSA-N 0.000 claims 1
- GAPABQQJKTWUMI-UHFFFAOYSA-N 2-[3-bromo-5-(trifluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NC=C(C=1)C(F)(F)F)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl GAPABQQJKTWUMI-UHFFFAOYSA-N 0.000 claims 1
- NIEZRHPGISPNOD-UHFFFAOYSA-N 2-[3-bromo-5-(trifluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NC=C(C=1)C(F)(F)F)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1Cl)Cl NIEZRHPGISPNOD-UHFFFAOYSA-N 0.000 claims 1
- JGCXNCLDULROCN-UHFFFAOYSA-N 2-[3-bromo-5-(trifluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NC=C(C=1)C(F)(F)F)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1F)F JGCXNCLDULROCN-UHFFFAOYSA-N 0.000 claims 1
- BMTFTWCNNYIPLT-UHFFFAOYSA-N 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyl-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound ClC=1C(=NC=C(C=1)C(F)(F)F)SCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl BMTFTWCNNYIPLT-UHFFFAOYSA-N 0.000 claims 1
- DIPMLKVAMDABNT-UHFFFAOYSA-N 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyl-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound ClC=1C(=NC=C(C=1)C(F)(F)F)SCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1Cl)Cl DIPMLKVAMDABNT-UHFFFAOYSA-N 0.000 claims 1
- ZIWBFXVQIOEAEJ-UHFFFAOYSA-N 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyl-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound ClC=1C(=NC=C(C=1)C(F)(F)F)SCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1F)F ZIWBFXVQIOEAEJ-UHFFFAOYSA-N 0.000 claims 1
- YLORCUFFZAQINL-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NN(C=1C(F)(F)F)C)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl YLORCUFFZAQINL-UHFFFAOYSA-N 0.000 claims 1
- STQGIYIRFFPBHW-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NN(C=1C(F)(F)F)C)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1Cl)Cl STQGIYIRFFPBHW-UHFFFAOYSA-N 0.000 claims 1
- GAPVFDFCXGUEHP-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NN(C=1C(F)(F)F)C)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1F)F GAPVFDFCXGUEHP-UHFFFAOYSA-N 0.000 claims 1
- LGORDOGBBIEGEN-UHFFFAOYSA-N 2-[4-bromo-2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C(=NN(C=1OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl)C)C(F)(F)F LGORDOGBBIEGEN-UHFFFAOYSA-N 0.000 claims 1
- VBYZRGMDNBWJPW-UHFFFAOYSA-N 2-[4-bromo-2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CN1N=C(C(Br)=C1OCC(=O)N1CCC(CC1)C1=NC(=CS1)C1=NOC(C1)C1=C(Cl)C=CC=C1Cl)C(F)(F)F VBYZRGMDNBWJPW-UHFFFAOYSA-N 0.000 claims 1
- CXJUSNADEBCGBE-UHFFFAOYSA-N 2-[5-(difluoromethyl)-1-methylpyrazol-3-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound FC(C1=CC(=NN1C)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl)F CXJUSNADEBCGBE-UHFFFAOYSA-N 0.000 claims 1
- ORDFXCLQBKYGBM-UHFFFAOYSA-N 2-[5-(difluoromethyl)-1-methylpyrazol-3-yl]oxy-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound FC(C1=CC(=NN1C)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1F)F)F ORDFXCLQBKYGBM-UHFFFAOYSA-N 0.000 claims 1
- LLECSVIHNATRSZ-UHFFFAOYSA-N 2-[5-bromo-3-(trifluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,4,6-trichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C=C(C(=NC=1)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=C(C=C1Cl)Cl)Cl)C(F)(F)F LLECSVIHNATRSZ-UHFFFAOYSA-N 0.000 claims 1
- IOLXHQNUGHSXSG-UHFFFAOYSA-N 2-[5-bromo-3-(trifluoromethyl)pyridin-2-yl]oxy-1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound BrC=1C=C(C(=NC=1)OCC(=O)N1CCC(CC1)C=1SC=C(N=1)C1=NOC(C1)C1=C(C=CC=C1Cl)Cl)C(F)(F)F IOLXHQNUGHSXSG-UHFFFAOYSA-N 0.000 claims 1
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- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 230000007330 shade avoidance Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- KAVUKAXLXGRUCD-UHFFFAOYSA-M sodium trifluoromethanesulfinate Chemical compound [Na+].[O-]S(=O)C(F)(F)F KAVUKAXLXGRUCD-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- QTZZYFLLQVLUNF-UHFFFAOYSA-N sodium;lithium Chemical compound [Li].[Na+] QTZZYFLLQVLUNF-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLGKMJFDRZHAEV-UHFFFAOYSA-N tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(C=O)=CS1 XLGKMJFDRZHAEV-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000006692 trifluoromethylation reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000011514 vinification Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
La présente invention concerne un composé de formule I et son procédé de préparation, dans la formule, R2, T, L1, A, G, J, n, W, Z et Z1 sont chacun tels que définis dans la description. L'invention concerne également une combinaison et une composition comprenant le composé de formule I.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201711031859 | 2017-09-08 | ||
| IN201711031859 | 2017-09-08 | ||
| PCT/IB2018/056581 WO2019048989A1 (fr) | 2017-09-08 | 2018-08-29 | Nouveaux composés hétérocycliques fongicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3073637A1 true CA3073637A1 (fr) | 2019-03-14 |
Family
ID=63713930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3073637A Pending CA3073637A1 (fr) | 2017-09-08 | 2018-08-29 | Nouveaux composes heterocycliques fongicides |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20200281202A1 (fr) |
| EP (1) | EP3679035A1 (fr) |
| JP (1) | JP2020533303A (fr) |
| KR (1) | KR20200105652A (fr) |
| CN (1) | CN111655687A (fr) |
| AR (1) | AR112795A1 (fr) |
| AU (1) | AU2018330784B2 (fr) |
| BR (1) | BR112020004356A2 (fr) |
| CA (1) | CA3073637A1 (fr) |
| CO (1) | CO2020002396A2 (fr) |
| MX (1) | MX2020002449A (fr) |
| TW (1) | TW201920164A (fr) |
| WO (1) | WO2019048989A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR120376A1 (es) | 2019-11-11 | 2022-02-09 | Pi Industries Ltd | Heteroaril piperidiniletanonas sustituidas con actividad fungicida |
| UY38940A (es) | 2019-11-11 | 2021-06-30 | Pi Industries Ltd | Nuevas piridiniloxi piperidiniletanonas sustituidas |
| UY38941A (es) * | 2019-11-11 | 2021-06-30 | Pi Industries Ltd | Nuevas sulfiliminas o sulfoximinas que contienen compuestos heterocíclicos fungicidas |
| TW202236965A (zh) | 2020-12-15 | 2022-10-01 | 印度商皮埃企業有限公司 | 包含哌啶噻唑化合物之新穎農業化學組成物 |
| AR125834A1 (es) | 2021-05-15 | 2023-08-16 | Pi Industries Ltd | Composición agroquímica que comprende compuestos de piperidin-tiazol |
| AR126600A1 (es) | 2021-07-29 | 2023-10-25 | Pi Industries Ltd | Compuestos novedosos de estireno y un proceso para la preparación de los mismos |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670543B1 (de) * | 1966-12-03 | 1971-07-01 | Degussa | Substituierte 2-Morpholino-4-piperazino-6-amino-s-triazine |
| AU1590501A (en) * | 1999-11-12 | 2001-06-06 | Merck & Co., Inc. | Aliphatic hydroxy substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents |
| CA2507707C (fr) | 2002-12-03 | 2011-06-21 | Axys Pharmaceuticals, Inc. | Derives de 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine utilises en tant qu'inhibiteurs du facteur viia |
| CN101128435A (zh) | 2004-12-27 | 2008-02-20 | 阿斯利康(瑞典)有限公司 | 作为代谢型谷氨酸受体激动剂用于治疗神经病学及精神病学病症的吡唑酮化合物 |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
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| AP2015008591A0 (en) * | 2012-12-11 | 2013-07-31 | Takeda Pharmaceutical | Heterocyclic compounds |
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| BR112016021869A2 (pt) | 2014-03-24 | 2017-10-24 | Bayer Cropscience Ag | derivados de fenilpiperidinacarboxamida como fungicidas |
| WO2016024350A1 (fr) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | Composés cycliques à 11 éléments condensés et fongicides pour l'agriculture et l'horticulture les contenant |
| US20180317488A1 (en) | 2015-11-03 | 2018-11-08 | Basf Se | Use of Substituted Oxadiazoles for Combating Phytopathogenic Fungi |
| WO2017109855A1 (fr) | 2015-12-22 | 2017-06-29 | 株式会社エス・ディー・エス バイオテック | Composé thiazole et germicide agricole et horticole le comprenant |
| WO2017109858A1 (fr) | 2015-12-22 | 2017-06-29 | 株式会社エス・ディー・エス バイオテック | Composé cyclique à 11 éléments condensé et germicide pour l'agriculture et l'horticulture le contenant |
| CN108601353B (zh) | 2016-02-08 | 2024-04-05 | 高文作物保护公司 | 杀菌性组合物 |
-
2018
- 2018-08-29 MX MX2020002449A patent/MX2020002449A/es unknown
- 2018-08-29 JP JP2020513695A patent/JP2020533303A/ja active Pending
- 2018-08-29 US US16/644,978 patent/US20200281202A1/en not_active Abandoned
- 2018-08-29 EP EP18779766.7A patent/EP3679035A1/fr not_active Withdrawn
- 2018-08-29 KR KR1020207009663A patent/KR20200105652A/ko not_active Ceased
- 2018-08-29 WO PCT/IB2018/056581 patent/WO2019048989A1/fr not_active Ceased
- 2018-08-29 AU AU2018330784A patent/AU2018330784B2/en not_active Ceased
- 2018-08-29 CA CA3073637A patent/CA3073637A1/fr active Pending
- 2018-08-29 BR BR112020004356-7A patent/BR112020004356A2/pt not_active Application Discontinuation
- 2018-08-29 CN CN201880071012.XA patent/CN111655687A/zh active Pending
- 2018-09-07 AR ARP180102550A patent/AR112795A1/es unknown
- 2018-09-07 TW TW107131544A patent/TW201920164A/zh unknown
-
2020
- 2020-03-03 CO CONC2020/0002396A patent/CO2020002396A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112020004356A2 (pt) | 2020-12-01 |
| KR20200105652A (ko) | 2020-09-08 |
| CN111655687A (zh) | 2020-09-11 |
| AU2018330784B2 (en) | 2022-11-17 |
| US20200281202A1 (en) | 2020-09-10 |
| EP3679035A1 (fr) | 2020-07-15 |
| JP2020533303A (ja) | 2020-11-19 |
| WO2019048989A1 (fr) | 2019-03-14 |
| MX2020002449A (es) | 2020-11-06 |
| CO2020002396A2 (es) | 2020-07-31 |
| TW201920164A (zh) | 2019-06-01 |
| AR112795A1 (es) | 2019-12-11 |
| AU2018330784A1 (en) | 2020-03-12 |
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